Isobutyraldehyde → HCID 54168338, compound

HRID 880420Notes

Reaction equation

HRID 880420 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6][C:7]#[N:8])=[O:5].[CH:9](=O)[CH:10]([CH3:12])[CH3:11]>C(O)(=O)C.O.N1CCCCC1>[C:7]([C:6](=[CH:9][CH:10]([CH3:12])[CH3:11])[C:4]([O:3][CH2:2][CH3:1])=[O:5])#[N:8]

Participants

6

Reactant 2

HCID 6561IsobutyraldehydeHCID 7764Ethyl cyanoacetate

Product 1

HCID 54168338HCID 54168338, compoundYield 43.9%

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of piperidine (0.3 mL, 3.04 mmol) in acetic acid (3 mL) was added to a solution of ethyl cyano acetate (10 g, 88.50 mmol) and isobutyraldehyde (9.35 g, 0.13 mol) in acetic acid at room temperature. The reaction mixture was allowed to stand for 24 h at room temperature, then diluted with water (50 mL) and extracted with ether (3×50 mL). The combined ether layers were washed with saturated bicarbonate solution, water, and brine and the organics were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude compound. Purification by vacuum distillation (95° C. at 0.1 mm Hg) afforded ethyl 2-cyano-4-methyl-pent-2-enoate (6.5 g, 30%) as a liquid.

Workup

  1. extractionextracted with ether (3×50 mL)
  2. washThe combined ether layers were washed with saturated bicarbonate solution, water, and brine
  3. dry with materialthe organics were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude compound
  6. customPurification
  7. distillationby vacuum distillation (95° C. at 0.1 mm Hg)

Sources & evidence

ORD record
ord-30d04bfd35874d59bec03a29893d4528
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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